1,2-Dichloroethane → Methyl 3-[(3-{[3-(6-{[(2E)-1-(4-methoxyphenyl)-2-methyl-1-phenylpenta-2,4-dienyl]amino}hexanoyl)pyrrolo[4,5-e]indolin-7-yl]carbonyl}pyrrolo[4,5-e]indolin-7-yl)carbonyl]pyrrolo[4,5-e]indoline-7-carboxylate

HRID 966463Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([N:28]2[C:39]3[C:31](=[C:32]4[C:36](=[CH:37][CH:38]=3)[NH:35][CH:34]([C:40](O)=[O:41])[CH2:33]4)[CH:30]=[CH:29]2)=[O:27])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[CH2:13])[CH:11]=[CH2:12])=[CH:5][CH:4]=1.[CH:43]1[C:47]2=[C:48]3[C:52](=[CH:53][CH:54]=[C:46]2[NH:45][CH:44]=1)[NH:51][CH:50]([C:55]([N:57]1[C:68]2[C:60](=[C:61]4[C:65](=[CH:66][CH:67]=2)[NH:64][CH:63]([C:69]([O:71][CH3:72])=[O:70])[CH2:62]4)[CH:59]=[CH:58]1)=[O:56])[CH2:49]3.[C:73](O)(C(F)(F)F)=O.C(Cl)CCl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([N:28]2[C:39]3[C:31](=[C:32]4[C:36](=[CH:37][CH:38]=3)[NH:35][CH:34]([C:40]([N:45]3[C:46]5[C:47](=[C:48]6[C:52](=[CH:53][CH:54]=5)[NH:51][CH:50]([C:55]([N:57]5[C:68]7[C:60](=[C:61]8[C:65](=[CH:66][CH:67]=7)[NH:64][CH:63]([C:69]([O:71][CH3:72])=[O:70])[CH2:62]8)[CH:59]=[CH:58]5)=[O:56])[CH2:49]6)[CH:43]=[CH:44]3)=[O:41])[CH2:33]4)[CH:30]=[CH:29]2)=[O:27])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)/[C:10](/[CH3:13])=[CH:11]/[CH:12]=[CH2:73])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 9 (213 mg, 0.36 mmol) and methyl 3-(pyrrolo[4,5-e]indolin-7-ylcarbonyl)pyrrolo[4,5-e]indoline-7-carboxylate (which had been prepared by TFA deprotection of 182 mg of the corresponding t-Boc precursor, Boger et al., supra) in 50 ml of anhydrous DMF was added EDC (200 mg). The reaction was stirred for 20 h 25° C. The resultant precipitate was collected by filtration, then washed with MeOH and ether. Drying under vacuum afforded 313 mg (90%) of the desired product as an off-white solid.

Workup

filtrationThe resultant precipitate was collected by filtration
washwashed with MeOH and ether
customDrying under vacuum

Sources & evidence

ORD record: ord-368752bb5502487ea93d4b287c01f60c
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951930B2

Reaction notes

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